Among them was 24-year-old construction worker Gerardo Lopez Arellano, one of nearly 11,200 illegal immigrants deported this year through Chicago, the location of a field office for a six-state region for Immigration and Customs Enforcement.
The number of people deported each year in the region that includes Illinois, Indiana, Kansas, Kentucky, Missouri and Wisconsin has nearly doubled since 2004, according to numbers released Thursday by ICE. About 6,600 people were deported through the fiscal year ending Sept. 30, 2004.
Deportations have also increased nationwide. Nearly 350,000 immigrants were deported in the U.S. through Sept. 30, 2008, compared with about 174,000 in the same period in 2004.
The trend is expected to continue. But experts and immigration officials aren't certain whether deportations - which affect less than 3 percent of the estimated 12 million illegal immigrants living in the U.S. this year - are an effective means of controlling illegal immigration.
It wasn't a factor for Arellano, a construction worker in suburban Chicago and Wisconsin who was deported twice before this year.
"I'll probably be back," he told The Associated Press hours before taking off in the white 737 jet.
Since its creation in 2003, ICE has touted its enforcement of immigration laws and the aggressive tactics agents use. For example, the agency has arrested tens of thousands in its Fugitive Operations Program, which dismantles transnational gangs.
The agency also has more resources than years past. Its budget was $5.58 billion this fiscal year, up from $3.56 billion in 2005, according to ICE's Web site.
In Chicago, federal officials have recently increased the frequency of Justice Prisoner and Alien Transportation System, or JPATS, flights leaving Chicago to twice from once a week.
"We made a commitment to the American people to embark on an ambitious enforcement strategy aimed at securing our borders and strengthening our nation's immigration system," Julie Myers, Homeland Security Assistant Secretary for ICE, said in a statement.
But in an interview earlier this year with The Associated Press, she said it's unclear if deportations are an effective means of stopping people from coming into the country illegally.
"It's too early to take a comprehensive view," Myers said. "We'll have to look a few years from now."
The majority of deported illegal immigrants in the six-state Midwest area are from Mexico. More than half, about 6,800, have not been accused of crimes.
Arellano, an admitted gang member, has a criminal record. He was charged with battery in 2006 and convicted of armed robbery last year, factors which will likely keep him from getting U.S. citizenship.
"When someone is deported ... we tell them the consequences," said Sylvia Manno with ICE's field operations in Chicago. "If they chose to come back, it's a choice they are making."
The number of deportations has increased in part due to the failure of new comprehensive immigration reform, according to James Ziglar, a fellow at the Migration Policy Institute and former Immigration and Naturalization Service Commissioner.
"If people want to come, there's a job, they need a job and they can't get here legally because the system doesn't accommodate a real flow of people, then they're going to come and take the chance," he said. "The risk of getting caught is a risk that they take."
Luis Armando Jimenez-Gonzalez, 20, who immigrated illegally to be with his fiancee who is a U.S. citizen, thought it was worth the risk.
"I came here to work, to have a better chance," he said.
Jimenez-Gonzalez, who also has a criminal record with a 2007 burglary conviction, worked in construction around Chicago. He was deported on the same flight as Arellano, but planned to stay with family in Mexico.
"It causes a lot of pain to come here," he said.
Some immigrant rights advocates say the increased deportation aren't effective and tear apart families who have mixed immigration status.
"Enforcement-only measures over the past decades have not worked in solving the problem of undocumented immigration in this country and will continue to be a failed policy on its own," Joshua Hoyt, the executive director of Illinois Coalition for Immigrant and Refugee Rights, said Thursday.
Arellano, who grew up near the Texas border, has several siblings who are U.S. citizens. He was born while his mother visited Mexico.
"I was supposed to be born in Texas, but I came out earlier," he said. "I haven't got any family in Mexico."
On the day of their deportations, Arellano and Jimenez-Gonzalez arrived at a suburban Chicago processing center with 50 other men, were handcuffed and interviewed by the Mexican Consulate.
The mood oscillated between somber and celebratory.
The men's belongings were placed in clear plastic bags. Some were filled with clothes, cowboy boots and socks. Another was packed with Bibles.
On the bus to O'Hare and their flight home, several men spontaneously started singing a popular Mexican folk song: "Mexico lindo y querido/Si muero lejos de ti/Que digan que estoy dormido y que me traigan aqui."
The lyrics translate to, "Mexico, dear and beautiful/If I die far from you/ Let them say that I'm asleep and return me to you."